The Rebooting Show

Mike White built Greater Long Island from a one-man blog in Patchogue into a regional news brand spanning Suffolk and Nassau counties. A veteran of the New York Post and Daily News, Mike took a scrappy, bootstrapped approach—publishing five stories a day, focusing on what neighbors actually care about, and treating advertisers like partners. We talk about how hustle, service journalism, and local roots can sustain media businesses when so many others are shrinking.

David Bank left the Wall Street Journal after a long run covering tech and philanthropy and assigned himself to a new beat in impact investing, a world of private capital being directed toward social good that legacy outlets largely ignored. That journalistic instinct grew into ImpactAlpha, which over the past decade has grown into what David calls the “hometown newspaper” for the “agents of impact”: investors, entrepreneurs, and institutions rethinking finance.

In this conversation, we talk about the messy reality of building a media company from scratch — from early sponsorships to subscription revenue, near-acquisitions that never happened, and raising money from mission-aligned investors. David also reflects on why the best publications start in overlooked niches, and why persistence is the real moat.

Louise Story, CEO of Atlas Obscura and veteran of The Wall Street Journal and The New York Times, joins me to talk about steering a beloved travel brand into its next chapter. We discuss her decision to wind down the in-house experiences business, why brand partnerships — especially with tourism bureaus — are now the company’s core revenue stream, and how she plans to turn Atlas Obscura’s community into the foundation for a robust travel-planning app. Louise also shares how her product background shapes her approach and why building direct audience relationships is critical in an era of search decline and AI disruption.

Adi Ignatius, editor-at-large of Harvard Business Review, discusses how HBR is expanding beyond traditional subscriptions with the launch of HBR Executive, a $700 premium tier aimed at senior leaders. We talk about the shift from volume to value in media, the importance of ARPU, the tension between brand legacy and innovation, and how publishers can better monetize the most valuable parts of their audience.

Variety co-editors-in-chief Cynthia Littleton and Ramin Setoodeh joined me to discuss how they strike this balance. We talk about how you treat publications as bigger brands, why print still matters in these models, the changing nature of celebrity in a creator era, how Variety builds franchises like Actors on Actors and the challenges facing the entertainment industry.

Substack's recent funding got a lot of attention for the headline valuation number, as all fundings do, but it's more interesting to examine what its new investment and investors say about the direction of the company. In this episode, I'm joined by Anonymous Banker to break down where Substack goes next and why OnlyFans is a better comp for its aspirations than YouTube.

Of all the areas AI is poised to overturn, marketing is at the top of the list. In truth, Silicon Valley has long held marketing is low esteem. Google CEO Eric Schmidt once sniffed that brand marketing is "the last bastion of unaccountable corporate spending." The mathification of marketing will go into hyperdrive, as AI is used to create some kind of agentic ecosystem of bots persuading bots. All of this is great scifi to Anonymous Brand Marketer, a Fortune 500 marketer who sees as much BS as promise in AI's application to marketing. ABM sees it both rationalizing and driving efficiencies in performance marketing while leading to a mini-resurgence in the kinds of brand marketing that connects to humans in ways that a Salesforce agent cannot.

Steve Grove spent over a decade inside Big Tech before returning home to Minnesota to run the Star Tribune. In this episode, we talk about what it takes to rebuild a local newspaper into a modern civic institution. Grove discusses why he left Google, how he’s restructured the Star Tribune’s newsroom and business model, and why local relevance—not scale—is the bet. From rebranding the paper and redesigning its digital products to narrowing its editorial focus and launching new revenue streams, Grove is trying to prove there’s a path forward for legacy news.

Generative AI is upending the long-standing relationship between publishers and the platforms that distribute their content. As tools like ChatGPT and Google’s AI Overviews deliver direct answers, the incentive to click through to publisher sites is disappearing. In this episode, I talk with Annelies Jansen, chief business officer at ProRata, about the need for a new economic model—one that accounts for how publisher content is used and ensures creators get paid. We discuss the risks of a bifurcated media ecosystem, how attribution can serve as the basis for compensation, and what a fair trade in the AI era might actually look like.

On this week’s episode of The Rebooting Show, I spoke with Vox Media president of revenue and growth Ryan Pauley about how the publisher has become a podcasting juggernaut, with Pivot, Decoder and Today Explained franchises. Ryan discusses the “Lego approach” that snaps together different business models, with some podcasts as owned and operated and others as partnerships. We also get into the rebundling and how media companies like Vox can link with creators to provide the sales and distribution infrastructure most independent media operators will not build.